5 Charming Small Towns Within a 2-hour Drive of Big Cities

Discover America’s Charming Small Towns TODAY!

We all love traveling to popular, well-known destinations in the US. But as tourism is starting to pick up again, and prices seem to be skyrocketing, you might prefer a weekend getaway that’s not too far from home.

A place where you’re close to all the action without being smack-dab in the middle of it. Luckily we went on the hunt for the most charming small towns in our country but within close driving distance of big cities. And we know what you might be thinking.

Most small towns are just stop-off points to get to other places, right? Not the ones we found! These charming places are incredible destinations in and of themselves, offering unique opportunities and a charm you probably won’t find in their bordering big cities.

So without further ado, here are our 5 favorite charming small towns that are a hop, skip, and a jump away from America’s big cities!

Baileys Harbor and Fish Creek, Wisconsin

Near: Green Bay
Population: 1,036

Just an hour’s drive away from the airport in Green Bay and a short drive from each other across the peninsula, these two charming small towns are the perfect getaway to visit state parks, lighthouses, and observatories.

Peninsula State Park in Fish Creek offers you 4,000 acres of recreation, and the New Eagle Tower there is Wisconsin’s first accessible observation tower that has spectacular views of the area’s water. There’s no shortage of seasonal activities, either.

You can experience everything from snowshoeing to parasailing. If you’re a fan of camping under the stars, you’ll love getting lost in nature and vacationing with the whole family in an affordable way.

And if you venture across the peninsula to Baileys Harbor, you’ll be able to look out over Lake Michigan. While here, hop on a hay wagon, and it’ll take you to the Cana Island Lighthouse.

Nowadays, it has become an interesting museum, and you can even climb to the top. Nature lovers will also love this charming small town because they can go on a leisurely hike through The Ridges Sanctuary to learn all about the topography of this remarkable region.

Leadville, Colorado

Near: Denver
Population: 2,693

A mere hour and 45 minutes away from the city of Denver, this historic, charming small town sits at 10,152ft, making it the highest city in the United States. It’s also home to the highest marathon in our country.

The area is a playground for outdoor enthusiasts and athletes, and the area also is rich in mining history. It’s practically an untouched mountain town. The biggest draw of Leadville is that it’s off the beaten path. you won’t find many commercialized specialties.

What they do have, however, are adorable locally-owned restaurants and shops. The best time to visit is in winter to enjoy the family-friendly slopes of Ski Cooper, that’s just 10 miles outside of town, and an annual skijoring festival.

You’ll get to see horses pull skiers down the town’s main street through a snowy obstacle course of hoops, jumps, and gates.

Brewster, Massachusetts

Near: Boston
Population: 9,820

Even though Cape Cod has no shortage of charming small towns, Brewster stands out for its long history. It was established in 1659 and has dramatic architecture and wide-open natural preserves.

With many miles of secluded bay-side beaches and over 5,000 acres of conservation land, including 80 sparkling kettle ponds originating from glaciers, it’s considered the area’s prime eco-tourism destination.

The charming small town is also a fantastic stop for bike lovers, with the Cape Cod Rail Trail that links Brewster to five towns. Overall, for folks who love the great outdoors and being in nature, Brewster is a terrific place to live in and visit.

Once known as “the sea captain’s town” due to the large number of rich ship captains who lived here, this town is still striped with lovely waterfront estates, many of which now operate as lodgings.

Mosier, Oregon

Near: Portland
Population: 451

Visiting this small riverfront town, you’d never guess that it was just an hour away from the big city lights of Portland. Unless, of course, you were to go on a weekend.

When Friday rolls around, this part of the Columbia River Gorge, the largest national scenic area in our country, gets flooded with people who live in the city who make the drive to windsurf, hike, purchase local cider, and enjoy the amazing restaurants and wineries.

You’ll discover that the close-knit community is very inviting and welcoming to everyone who comes here. For now, this charming small town remains less well-known than the bigger nearby towns, like Hood River. But that won’t last forever.

A younger population seems to be slowly discovering Mosier, reviving it. But so far, the area is still keeping its small-town charm and values.

…If you choose to visit this charming town, be sure to pack your camera to capture the scenery!

Leiper’s Fork, Tennessee

Near: Nashville
Population: 650

If you drive forty minutes south of Nashville, you’ll be greeted by this Hallmark movie town that has unique art galleries, wine from Tennessee whiskey barrels, and a honky-tonk joint with the kind of talent you’d expect from a town so close to “Music City.”

You can choose to stay in one of this charming small town’s lovely cottages with architecture that holds true to the historic nature of the area while offering a long list of luxuries.

To get a sense of the culture, visit The Copper Fox, a gallery with paintings, sculptures, handbags, jewelry, and many decorative home decor. You can stay a while to chat with an artist and go home with a one-of-a-kind catch.

And just a few doors down, Leiper’s Creek Gallery manages to perfectly balance incredible pieces of art with approachable, Southern hospitality. Across the street, unwind at Wines in the Fork. You’ll enjoy sophisticated wine aged in Tennessee whiskey oak barrels.

Finally, finish your day in this charming small town at Puckett’s, a one-time general store that’s now a music venue and restaurant where the music is top-notch.

Did you enjoy reading about these charming small towns? Be sure to let us know in the comments section!

And if you liked this article, we have another one we think you’ll love. Check out: Route 66: 8 Incredible Sights You Can’t Miss